Identification
NameUC-781
Accession NumberDB05871  (DB08679)
TypeSmall Molecule
GroupsInvestigational
Description

UC-781 is a thiocarboxanilide non-nucleoside reverse transcriptase inhibitor (NNRTI). It is a topical microbicide targeted against the AIDS virus.

Structure
Thumb
SynonymsNot Available
External IDs NSC-675186 / UC781
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIL7K247H29H
CAS number178870-32-1
WeightAverage: 335.848
Monoisotopic: 335.074677222
Chemical FormulaC17H18ClNO2S
InChI KeyYZHIXLCGPOTQNB-UHFFFAOYSA-N
InChI
InChI=1S/C17H18ClNO2S/c1-11(2)6-8-21-16-10-13(4-5-15(16)18)19-17(22)14-7-9-20-12(14)3/h4-7,9-10H,8H2,1-3H3,(H,19,22)
IUPAC Name
N-{4-chloro-3-[(3-methylbut-2-en-1-yl)oxy]phenyl}-2-methylfuran-3-carbothioamide
SMILES
CC(C)=CCOC1=C(Cl)C=CC(NC(=S)C2=C(C)OC=C2)=C1
Pharmacology
Indication

Investigated for use/treatment in HIV infection.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

UC-781 is an HIV non-nucleoside reverse transcriptase inhibitor (NNRTI) that has shown in vitro to be very active specifically against HIV-1. UC-781 exhibits synergy with the NRTI zidovudine in vitro.[12] The combination of UC-781 and another candidate microbicide, cellulose acetate 1,2-benzenedicarboxylate, resulted in effective synergy for inhibition of HIV-1 in vitro and in peripheral blood mononuclear cells

TargetKindPharmacological actionActionsOrganismUniProt ID
Gag-Pol polyproteinProteinunknownNot AvailableHIV-1P03366 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Patton DL, Sweeney YT, Balkus JE, Rohan LC, Moncla BJ, Parniak MA, Hillier SL: Preclinical safety assessments of UC781 anti-human immunodeficiency virus topical microbicide formulations. Antimicrob Agents Chemother. 2007 May;51(5):1608-15. Epub 2007 Mar 12. [PubMed:17353240 ]
  2. Hossain MM, Parniak MA: In vitro microbicidal activity of the nonnucleoside reverse transcriptase inhibitor (NNRTI) UC781 against NNRTI-resistant human immunodeficiency virus type 1. J Virol. 2006 May;80(9):4440-6. [PubMed:16611904 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0123 mg/mLALOGPS
logP4.07ALOGPS
logP5.1ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.85ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area34.4 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.63 m3·mol-1ChemAxon
Polarizability35.48 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.868
Caco-2 permeable+0.5624
P-glycoprotein substrateNon-substrate0.7838
P-glycoprotein inhibitor IInhibitor0.7317
P-glycoprotein inhibitor IINon-inhibitor0.7672
Renal organic cation transporterNon-inhibitor0.7839
CYP450 2C9 substrateNon-substrate0.7202
CYP450 2D6 substrateNon-substrate0.7351
CYP450 3A4 substrateSubstrate0.5916
CYP450 1A2 substrateInhibitor0.8428
CYP450 2C9 inhibitorInhibitor0.7788
CYP450 2D6 inhibitorNon-inhibitor0.7976
CYP450 2C19 inhibitorInhibitor0.8637
CYP450 3A4 inhibitorInhibitor0.6668
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.97
Ames testNon AMES toxic0.5371
CarcinogenicityNon-carcinogens0.7322
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.5074 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7043
hERG inhibition (predictor II)Non-inhibitor0.7358
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative ParentsPhenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Thioamides / Heteroaromatic compounds / Furans / Thiocarboxylic acid amides / Oxacyclic compounds / Thiocarbonyl compounds
SubstituentsPhenoxy compound / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Heteroaromatic compound / Furan
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
HIV-1
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spherical particles, recruiting the viral Env proteins, and packaging the genomic RNA via direct interactions with the RNA packaging sequence (Psi). Gag-Pol polyprotein may regulate its own translation, by...
Gene Name:
gag-pol
Uniprot ID:
P03366
Molecular Weight:
163287.51 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Drug created on November 18, 2007 11:28 / Updated on June 11, 2017 21:01